diff --git a/configure.py b/configure.py
index 379fb5bb06c413..909f99e5b001bd 100755
--- a/configure.py
+++ b/configure.py
@@ -1306,6 +1306,9 @@ def host_arch_win():
 
   return matchup.get(arch, 'ia32')
 
+def set_configuration_variable(configs, name, release=None, debug=None):
+  configs['Release'][name] = release
+  configs['Debug'][name] = debug
 
 def configure_arm(o):
   if options.arm_float_abi:
@@ -1620,7 +1623,9 @@ def configure_library(lib, output, pkgname=None):
       output['libraries'] += pkg_libs.split()
 
 
-def configure_v8(o):
+def configure_v8(o, configs):
+  set_configuration_variable(configs, 'v8_enable_v8_checks', release=1, debug=0)
+
   o['variables']['v8_enable_webassembly'] = 0 if options.v8_lite_mode else 1
   o['variables']['v8_enable_javascript_promise_hooks'] = 1
   o['variables']['v8_enable_lite_mode'] = 1 if options.v8_lite_mode else 0
@@ -1638,7 +1643,6 @@ def configure_v8(o):
   o['variables']['v8_enable_31bit_smis_on_64bit_arch'] = 1 if options.enable_pointer_compression else 0
   o['variables']['v8_enable_shared_ro_heap'] = 0 if options.enable_pointer_compression or options.disable_shared_ro_heap else 1
   o['variables']['v8_enable_extensible_ro_snapshot'] = 0
-  o['variables']['v8_enable_v8_checks'] = 1 if options.debug else 0
   o['variables']['v8_trace_maps'] = 1 if options.trace_maps else 0
   o['variables']['node_use_v8_platform'] = b(not options.without_v8_platform)
   o['variables']['node_use_bundled_v8'] = b(not options.without_bundled_v8)
@@ -2154,6 +2158,10 @@ def make_bin_override():
   'defines': [],
   'cflags': [],
 }
+configurations = {
+  'Release': { 'variables': {} },
+  'Debug': { 'variables': {} },
+}
 
 # Print a warning when the compiler is too old.
 check_compiler(output)
@@ -2181,7 +2189,7 @@ def make_bin_override():
 configure_library('ngtcp2', output, pkgname='libngtcp2')
 configure_library('sqlite', output, pkgname='sqlite3')
 configure_library('uvwasi', output, pkgname='libuvwasi')
-configure_v8(output)
+configure_v8(output, configurations)
 configure_openssl(output)
 configure_intl(output)
 configure_static(output)
@@ -2204,7 +2212,6 @@ def make_bin_override():
 # move everything else to target_defaults
 variables = output['variables']
 del output['variables']
-variables['is_debug'] = B(options.debug)
 
 # make_global_settings should be a root level element too
 if 'make_global_settings' in output:
@@ -2213,6 +2220,9 @@ def make_bin_override():
 else:
   make_global_settings = False
 
+# Add configurations to target defaults
+output['configurations'] = configurations
+
 output = {
   'variables': variables,
   'target_defaults': output,
@@ -2223,7 +2233,7 @@ def make_bin_override():
 print_verbose(output)
 
 write('config.gypi', do_not_edit +
-      pprint.pformat(output, indent=2, width=1024) + '\n')
+      pprint.pformat(output, indent=2, width=128) + '\n')
 
 write('config.status', '#!/bin/sh\nset -x\nexec ./configure ' +
       ' '.join([shlex.quote(arg) for arg in original_argv]) + '\n')
diff --git a/tools/v8_gypfiles/features.gypi b/tools/v8_gypfiles/features.gypi
index db9bda604bc176..6e21dac6d70ede 100644
--- a/tools/v8_gypfiles/features.gypi
+++ b/tools/v8_gypfiles/features.gypi
@@ -88,7 +88,6 @@
         'v8_enable_private_mapping_fork_optimization': 0,
       }],
     ],
-    'is_debug%': 0,
 
     # Variables from BUILD.gn
 
diff --git a/tools/v8_gypfiles/toolchain.gypi b/tools/v8_gypfiles/toolchain.gypi
index 98e738d0a81c53..9d1b0987167fc6 100644
--- a/tools/v8_gypfiles/toolchain.gypi
+++ b/tools/v8_gypfiles/toolchain.gypi
@@ -711,13 +711,7 @@
     'configurations': {
       'Debug': {
         'defines': [
-          'ENABLE_DISASSEMBLER',
-          'V8_ENABLE_CHECKS',
-          'OBJECT_PRINT',
           'DEBUG',
-          'V8_TRACE_MAPS',
-          'V8_ENABLE_ALLOCATION_TIMEOUT',
-          'V8_ENABLE_FORCE_SLOW_PATH',
         ],
         'conditions': [
           ['OS=="linux" and v8_enable_backtrace==1', {